Water → HCID 135939611, compound

HRID 1927280Notes

Reaction equation

HRID 1927280 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[CH:20]=[C:10]3[NH:11][C:12](=[O:19])[C:13]4[C:18]([N:9]3[N:8]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:2]1.I[CH:22]([CH3:24])[CH3:23].[H-].[Na+].O>O1CCOCC1>[CH:22]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]2[CH:20]=[C:10]3[NH:11][C:12](=[O:19])[C:13]4[C:18]([N:9]3[N:8]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:2]1)([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 135939599HCID 135939599, compound

Product 1

HCID 135939611HCID 135939611, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of EXAMPLE 19 (0.07 g, 0.3 mmol) and 2-iodopropane (0.09 mL, 0.9 mmol) in dioxane (2 mL) and was treated with sodium hydride (0.01 g, 0.4 mmol). The mixture was stirred overnight at 65° C., cooled to ambient temperature, treated with water and concentrated. The residue was purified by flash chromatography on silica gel with 10% methanol/dichloromethane to provide the title compound. 1H NMR (CD3OD) δ 8.21 (dd, J=8.0, 1.5 Hz, 1H), 8.11 (d, J=8.0 Hz, 1H), 7.81-7.87 (m, 1H), 7.42-7.47 (m, 1H), 5.88 (s, 1H), 3.21 (dt, J=11.3, 1.9, 1H), 2.99-3.10 (m, 2H), 2.92 (dt, J=13.2, 6.6 Hz, 1H), 2.51 (t, J=11.0 Hz, 1H), 2.38 (td, J=11.5, 2.8 Hz, 1H), 2.09 (ddd, J=9.0, 3.8, 3.7 Hz, 1H), 1.83-1.92 (m, 1H), 1.70-1.82 (m, 1H), 1.59 (qd, J=12.3, 4.0 Hz, 1H), 1.14-1.19 (m, 6H).

Workup

  1. temperaturecooled to ambient temperature
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography on silica gel with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-15d3130b74a84d35b8cf3f08c610a68b
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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